Secobarbital

Details

• Internal ID: a6eb9dc0-967d-4dd6-afba-3a368fdf8c94
• Taxonomy: Organoheterocyclic compounds > Diazines > Pyrimidines and pyrimidine derivatives > Pyrimidones > Barbituric acid derivatives
• IUPAC Name: 5-pentan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
• SMILES (Canonical): CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C
• SMILES (Isomeric): CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C
• InChI: InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
• InChI Key: KQPKPCNLIDLUMF-UHFFFAOYSA-N
• Popularity: 1,778 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₈N₂O₃
• Molecular Weight: 238.28 g/mol
• Exact Mass: 238.13174244 g/mol
• Topological Polar Surface Area (TPSA): 75.30 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.35
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Secobarbitone
• Quinalbarbitone
• Seconal
• Quinalbarbital
• Evronal
• Hypotrol
• Meballymal
• 76-73-3
• Immenox
• Secobarbitalum
• Somosal
• (+-)-Secobarbital
• Secobarbitale
• Somatarax
• 5-ALLYL-5-(1-METHYLBUTYL)BARBITURIC ACID
• (RS)-Secobarbital
• Secobarbital cii
• 5-Allyl-5-(1-methylbutyl)malonylurea
• Barbituric acid, 5-allyl-5-(1-methylbutyl)-
• 5-Allyl-5-(1-methylbutyl)barbiturate
• 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propenyl)-
• 5-pentan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
• CHEBI:9073
• 1P7H87IN75
• 5-Allyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
• Sodium quinalbarbitone
• Secobarbital sodium free acid
• DTXSID6044145
• 5-allyl-5-(1-methylbutyl)pyrimidine-2,4,6(1H,3H,5H)-trione
• 5-(1-methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
• Imesonal
• Trisomnin
• 5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
• secobarbital-natrium
• RefChem:884783
• DTXCID4024145
• N05CA06
• 200-982-2
• Secobarbitale [DCIT]
• Seotal
• Secobarbitalum [INN-Latin]
• Meballymalum
• Hyptran
• (+/-)-Secobarbital
• DEA No. 2315
• Sodium secobarbital
• 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propen-1-yl)-
• Secobarbital (1.0mg/ml in Methanol)
• Secobarbital (1mg/ml in Acetonitrile)
• Seconal (TN)
• HSDB 3182
• (+/-)-Quinalbarbitone
• Secobarbital suppository dosage form
• EINECS 200-982-2
• Secobarbital (USP/INN)
• Secobarbital [USP:INN]
• (+-)-5-Allyl-5-(1-methylbutyl)-barbituric acid
• BRN 0225330
• UNII-1P7H87IN75
• NCGC00247712-01
• Hyptran (Salt/Mix)
• Imesonal (Salt/Mix)
• Trisomnin (Salt/Mix)
• Immenoctal (Salt/Mix)
• BARBITURIC ACID, 5-ALLYL-5-(1-METHYLBUTYL)-, (+-)-
• SECOBARBITAL [INN]
• CHEMBL447
• SECOBARBITAL [HSDB]
• (.+/-.))-Secobarbital
• SECOBARBITAL [VANDF]
• SCHEMBL80734
• SECOBARBITAL [MART.]
• 5-24-09-00235 (Beilstein Handbook Reference)
• SECOBARBITAL [USP-RS]
• SECOBARBITAL [WHO-DD]
• GTPL7615
• SCHEMBL11110602
• Secobarbital, analytical standard
• Secobarbital, 1mg/ml in Methanol
• SECOBARBITAL [USP IMPURITY]
• VFA24397
• Secobarbital 0.1 mg/ml in Methanol
• Secobarbital 1.0 mg/ml in Methanol
• 5-(1-Methylbutyl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione
• 5-(pentan-2-yl)-5-(prop-2-en-1-yl)-pyrimidine-2,4,6(1H,3H,5H)-trione
• DB00418
• 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propenyl)-, (+-)-
• SECOBARBITAL SODIUM FREE ACID [MI]
• NS00010411
• S0223
• D00430
• Q414788
• Secobarbital suppository dosage form [DEA No. 2316]
• pyrimidine-2,4,6(1H,3H,5H)-trione, 5-allyl-5-(1-methylbutyl)-
• Secobarbital, United States Pharmacopeia (USP) Reference Standard
• 2,4,6(1H,3H,5H)-Pyrimidinitrione, 5-(1-methylbutyl)-5-(2-propenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9803	98.03%
Caco-2	+	0.5346	53.46%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.9429	94.29%
Subcellular localzation	Mitochondria	0.8002	80.02%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9402	94.02%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9795	97.95%
P-glycoprotein inhibitior	-	0.9706	97.06%
P-glycoprotein substrate	-	0.8855	88.55%
CYP3A4 substrate	-	0.6660	66.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	-	0.8902	89.02%
CYP2C9 inhibition	-	0.7679	76.79%
CYP2C19 inhibition	-	0.7353	73.53%
CYP2D6 inhibition	-	0.9276	92.76%
CYP1A2 inhibition	-	0.8707	87.07%
CYP2C8 inhibition	-	0.9698	96.98%
CYP inhibitory promiscuity	-	0.9176	91.76%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.6653	66.53%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9848	98.48%
Skin irritation	-	0.7788	77.88%
Skin corrosion	-	0.9230	92.30%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6931	69.31%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8463	84.63%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6443	64.43%
Acute Oral Toxicity (c)	II	0.6048	60.48%
Estrogen receptor binding	-	0.7109	71.09%
Androgen receptor binding	-	0.8549	85.49%
Thyroid receptor binding	-	0.6263	62.63%
Glucocorticoid receptor binding	-	0.7290	72.90%
Aromatase binding	-	0.8151	81.51%
PPAR gamma	-	0.8590	85.90%
Honey bee toxicity	-	0.8503	85.03%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9479	94.79%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL321	P14780	Matrix metalloproteinase 9	2643 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.91%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.56%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.50%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.27%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.14%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	89.33%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.41%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.26%	96.61%
CHEMBL321	P14780	Matrix metalloproteinase 9	85.98%	92.12%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.93%	91.11%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.98%	96.47%
CHEMBL255	P29275	Adenosine A2b receptor	82.17%	98.59%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.60%	92.88%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.30%	90.71%
CHEMBL1907	P15144	Aminopeptidase N	80.13%	93.31%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.08%	93.56%

Plants that contains it

• Paederia foetida

Cross-Links

• PubChem: 5193
• NPASS: NPC21848
• ChEMBL: CHEMBL447